JP4454225B2 - ラセミメタロセン錯体の製造方法 - Google Patents
ラセミメタロセン錯体の製造方法 Download PDFInfo
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- JP4454225B2 JP4454225B2 JP2002505794A JP2002505794A JP4454225B2 JP 4454225 B2 JP4454225 B2 JP 4454225B2 JP 2002505794 A JP2002505794 A JP 2002505794A JP 2002505794 A JP2002505794 A JP 2002505794A JP 4454225 B2 JP4454225 B2 JP 4454225B2
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- alkyl
- aryl
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 9
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims abstract description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 175
- 125000004432 carbon atom Chemical group C* 0.000 claims description 105
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 96
- 125000003118 aryl group Chemical group 0.000 claims description 84
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 75
- -1 respectively Chemical compound 0.000 claims description 72
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 229910052726 zirconium Inorganic materials 0.000 claims description 31
- 239000000460 chlorine Substances 0.000 claims description 27
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 26
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 26
- 229910052749 magnesium Inorganic materials 0.000 claims description 25
- 239000011777 magnesium Substances 0.000 claims description 25
- 229920006395 saturated elastomer Polymers 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
- 230000015572 biosynthetic process Effects 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 18
- 125000004122 cyclic group Chemical group 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 150000003254 radicals Chemical class 0.000 claims description 16
- 230000007704 transition Effects 0.000 claims description 16
- 229910052727 yttrium Inorganic materials 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 13
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 12
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 10
- 125000004407 fluoroaryl group Chemical group 0.000 claims description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 9
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 150000001340 alkali metals Chemical class 0.000 claims description 9
- 229910052732 germanium Inorganic materials 0.000 claims description 9
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- 239000010703 silicon Substances 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 229910052718 tin Inorganic materials 0.000 claims description 9
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910052719 titanium Inorganic materials 0.000 claims description 8
- 239000010936 titanium Substances 0.000 claims description 8
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229910052735 hafnium Inorganic materials 0.000 claims description 7
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 230000000737 periodic effect Effects 0.000 claims description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 5
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical group [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 5
- 229910052804 chromium Inorganic materials 0.000 claims description 5
- 239000011651 chromium Chemical group 0.000 claims description 5
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 5
- 150000002602 lanthanoids Chemical class 0.000 claims description 5
- 229910052750 molybdenum Inorganic materials 0.000 claims description 5
- 239000011733 molybdenum Chemical group 0.000 claims description 5
- 229910052758 niobium Inorganic materials 0.000 claims description 5
- 239000010955 niobium Chemical group 0.000 claims description 5
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical group [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052715 tantalum Inorganic materials 0.000 claims description 5
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical group [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 5
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical group [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 5
- 229910052721 tungsten Inorganic materials 0.000 claims description 5
- 239000010937 tungsten Chemical group 0.000 claims description 5
- 229910052720 vanadium Inorganic materials 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- KSCFJBIXMNOVSH-UHFFFAOYSA-N dyphylline Chemical group O=C1N(C)C(=O)N(C)C2=C1N(CC(O)CO)C=N2 KSCFJBIXMNOVSH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical group [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
- 239000003446 ligand Substances 0.000 abstract description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 abstract description 7
- 229910052723 transition metal Inorganic materials 0.000 abstract description 4
- 229940031826 phenolate Drugs 0.000 abstract description 3
- 150000003624 transition metals Chemical class 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 90
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 67
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
- 150000002431 hydrogen Chemical class 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 20
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 229910007926 ZrCl Inorganic materials 0.000 description 11
- 238000006467 substitution reaction Methods 0.000 description 11
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
- SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 description 10
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- PYADVBBPPYGPGF-UHFFFAOYSA-N 3,3-dimethylbutane-2,2-diamine Chemical compound CC(C)(C)C(C)(N)N PYADVBBPPYGPGF-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002879 Lewis base Substances 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 150000007527 lewis bases Chemical class 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011877 solvent mixture Substances 0.000 description 5
- 230000000707 stereoselective effect Effects 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 4
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical group [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 4
- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical group FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 102000015782 Electron Transport Complex III Human genes 0.000 description 3
- 108010024882 Electron Transport Complex III Proteins 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000006343 heptafluoro propyl group Chemical group 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 0 CC(C(C)C(C(C)(C1C2*C2)C2(C)CCCCC2)N)C1N Chemical compound CC(C(C)C(C(C)(C1C2*C2)C2(C)CCCCC2)N)C1N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- YFCIXLODLPGTEP-UHFFFAOYSA-J [Zr+4].C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)[O-].C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)[O-].C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)[O-].C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)[O-] Chemical compound [Zr+4].C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)[O-].C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)[O-].C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)[O-].C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)[O-] YFCIXLODLPGTEP-UHFFFAOYSA-J 0.000 description 2
- WWBBOLNIGORGDL-UHFFFAOYSA-J [Zr+4].CC1=C(C(=CC(=C1)C)C)[O-].CC1=C(C(=CC(=C1)C)C)[O-].CC1=C(C(=CC(=C1)C)C)[O-].CC1=C(C(=CC(=C1)C)C)[O-] Chemical compound [Zr+4].CC1=C(C(=CC(=C1)C)C)[O-].CC1=C(C(=CC(=C1)C)C)[O-].CC1=C(C(=CC(=C1)C)C)[O-].CC1=C(C(=CC(=C1)C)C)[O-] WWBBOLNIGORGDL-UHFFFAOYSA-J 0.000 description 2
- BPWVHTNZLKSWLZ-UHFFFAOYSA-J [Zr+4].CC1=CC=CC(C)=C1[O-].CC1=CC=CC(C)=C1[O-].CC1=CC=CC(C)=C1[O-].CC1=CC=CC(C)=C1[O-] Chemical compound [Zr+4].CC1=CC=CC(C)=C1[O-].CC1=CC=CC(C)=C1[O-].CC1=CC=CC(C)=C1[O-].CC1=CC=CC(C)=C1[O-] BPWVHTNZLKSWLZ-UHFFFAOYSA-J 0.000 description 2
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000005103 alkyl silyl group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000005104 aryl silyl group Chemical group 0.000 description 2
- 229910052790 beryllium Inorganic materials 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 150000001793 charged compounds Chemical class 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 2
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- SRAXOLZKHXOWQJ-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=C(C=CC=C12)C(C)C)CC)C1C(=CC2=C(C=CC=C12)C(C)C)CC)C Chemical compound C[Si](=[Zr](C1C(=CC2=C(C=CC=C12)C(C)C)CC)C1C(=CC2=C(C=CC=C12)C(C)C)CC)C SRAXOLZKHXOWQJ-UHFFFAOYSA-N 0.000 description 1
- AZDPJSQDGAHDLY-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=C(C=CC=C12)C1=CC=CC=C1)C1CCCCC1)C1C(=CC2=C(C=CC=C12)C1=CC=CC=C1)C1CCCCC1)C Chemical compound C[Si](=[Zr](C1C(=CC2=C(C=CC=C12)C1=CC=CC=C1)C1CCCCC1)C1C(=CC2=C(C=CC=C12)C1=CC=CC=C1)C1CCCCC1)C AZDPJSQDGAHDLY-UHFFFAOYSA-N 0.000 description 1
- PMGGPGYTYMYSSW-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=CC=C3C(=C12)C=CC=C3)C1=CC=CC=C1)C1C(=CC2=CC=C3C(=C12)C=CC=C3)C1=CC=CC=C1)C Chemical compound C[Si](=[Zr](C1C(=CC2=CC=C3C(=C12)C=CC=C3)C1=CC=CC=C1)C1C(=CC2=CC=C3C(=C12)C=CC=C3)C1=CC=CC=C1)C PMGGPGYTYMYSSW-UHFFFAOYSA-N 0.000 description 1
- ZVUOWHPNEAKYJV-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=CC=C3C(=C12)C=CC=C3)CC)C1C(=CC2=CC=C3C(=C12)C=CC=C3)CC)C Chemical compound C[Si](=[Zr](C1C(=CC2=CC=C3C(=C12)C=CC=C3)CC)C1C(=CC2=CC=C3C(=C12)C=CC=C3)CC)C ZVUOWHPNEAKYJV-UHFFFAOYSA-N 0.000 description 1
- MTADEDFCWKNPKF-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=CC=C3C(=C12)C=CC=C3)CCC)C1C(=CC2=CC=C3C(=C12)C=CC=C3)CCC)C Chemical compound C[Si](=[Zr](C1C(=CC2=CC=C3C(=C12)C=CC=C3)CCC)C1C(=CC2=CC=C3C(=C12)C=CC=C3)CCC)C MTADEDFCWKNPKF-UHFFFAOYSA-N 0.000 description 1
- QVGXPRAFPBPERW-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC=2CCCCC1=2)C)C1C(=CC=2CCCCC1=2)C)C Chemical compound C[Si](=[Zr](C1C(=CC=2CCCCC1=2)C)C1C(=CC=2CCCCC1=2)C)C QVGXPRAFPBPERW-UHFFFAOYSA-N 0.000 description 1
- BJNQGOCWLMDGCY-UHFFFAOYSA-N C[Si](=[Zr](C1C(CC2CC=C3C(=C12)C=CC=C3)C)C1C(CC2CC=C3C(=C12)C=CC=C3)C)C Chemical compound C[Si](=[Zr](C1C(CC2CC=C3C(=C12)C=CC=C3)C)C1C(CC2CC=C3C(=C12)C=CC=C3)C)C BJNQGOCWLMDGCY-UHFFFAOYSA-N 0.000 description 1
- YXJKDSUBJYUIBR-UHFFFAOYSA-N C[Si](=[Zr](C1C=C(C=C1C)C(C)(C)C)C1C=C(C=C1C)C(C)(C)C)C Chemical compound C[Si](=[Zr](C1C=C(C=C1C)C(C)(C)C)C1C=C(C=C1C)C(C)(C)C)C YXJKDSUBJYUIBR-UHFFFAOYSA-N 0.000 description 1
- HJONASBBJDDFNA-UHFFFAOYSA-N C[Si](=[Zr](C1C=C(C=C1C)C(C)(C)CC)C1C=C(C=C1C)C(C)(C)CC)C Chemical compound C[Si](=[Zr](C1C=C(C=C1C)C(C)(C)CC)C1C=C(C=C1C)C(C)(C)CC)C HJONASBBJDDFNA-UHFFFAOYSA-N 0.000 description 1
- JODWEPMBPFCAAH-UHFFFAOYSA-N C[Si](=[Zr](C1C=C(C=C1CC)C(C)(C)C)C1C=C(C=C1CC)C(C)(C)C)C Chemical compound C[Si](=[Zr](C1C=C(C=C1CC)C(C)(C)C)C1C=C(C=C1CC)C(C)(C)C)C JODWEPMBPFCAAH-UHFFFAOYSA-N 0.000 description 1
- KWVIZFHBKXSQRC-UHFFFAOYSA-N C[Si](C)=[Zr](C1C=CC2=C1CCCC2)C1C=CC2=C1CCCC2 Chemical compound C[Si](C)=[Zr](C1C=CC2=C1CCCC2)C1C=CC2=C1CCCC2 KWVIZFHBKXSQRC-UHFFFAOYSA-N 0.000 description 1
- FCSYHQWMXFGBSC-UHFFFAOYSA-N C[Si](C)=[Zr](C1C=Cc2ccccc12)C1C=Cc2ccccc12 Chemical compound C[Si](C)=[Zr](C1C=Cc2ccccc12)C1C=Cc2ccccc12 FCSYHQWMXFGBSC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical class ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N Dipicolinic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- UWCPYKQBIPYOLX-UHFFFAOYSA-N benzene-1,3,5-tricarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 UWCPYKQBIPYOLX-UHFFFAOYSA-N 0.000 description 1
- HPMLGNIUXVXALD-UHFFFAOYSA-N benzoyl fluoride Chemical compound FC(=O)C1=CC=CC=C1 HPMLGNIUXVXALD-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- PDPJQWYGJJBYLF-UHFFFAOYSA-J hafnium tetrachloride Chemical compound Cl[Hf](Cl)(Cl)Cl PDPJQWYGJJBYLF-UHFFFAOYSA-J 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- KJJBSBKRXUVBMX-UHFFFAOYSA-N magnesium;butane Chemical compound [Mg+2].CCC[CH2-].CCC[CH2-] KJJBSBKRXUVBMX-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 1
- YSTQWZZQKCCBAY-UHFFFAOYSA-L methylaluminum(2+);dichloride Chemical compound C[Al](Cl)Cl YSTQWZZQKCCBAY-UHFFFAOYSA-L 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000005634 peroxydicarbonate group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000011915 stereoselective alkylation Methods 0.000 description 1
- 238000011916 stereoselective reduction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- DJIFSIBYHXVGSS-UHFFFAOYSA-J zirconium(4+);tetraphenoxide Chemical class [Zr+4].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 DJIFSIBYHXVGSS-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10030638A DE10030638A1 (de) | 2000-06-29 | 2000-06-29 | Verfahren zur selektiven Herstellung racemischer Metallocenkomplexe |
| PCT/EP2001/007389 WO2002000672A1 (de) | 2000-06-29 | 2001-06-28 | Verfahren zur selektiven herstellung racemischer metallocenkomplexe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004501928A JP2004501928A (ja) | 2004-01-22 |
| JP4454225B2 true JP4454225B2 (ja) | 2010-04-21 |
Family
ID=7646554
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002505794A Expired - Fee Related JP4454225B2 (ja) | 2000-06-29 | 2001-06-28 | ラセミメタロセン錯体の製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6992204B2 (de) |
| EP (1) | EP1294734B1 (de) |
| JP (1) | JP4454225B2 (de) |
| CN (1) | CN1267441C (de) |
| AT (1) | ATE267205T1 (de) |
| AU (1) | AU2001285786A1 (de) |
| BR (1) | BR0112050A (de) |
| DE (2) | DE10030638A1 (de) |
| ES (1) | ES2219557T3 (de) |
| MX (1) | MXPA03000054A (de) |
| WO (1) | WO2002000672A1 (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7193099B2 (en) | 2002-10-25 | 2007-03-20 | Basell Polyolefine Gmbh | Racemoselective preparation of isolable ansa-metallocene biphenoxide complexes |
| DE10250062A1 (de) | 2002-10-25 | 2004-05-06 | Basell Polyolefine Gmbh | Verfahren zur racemoselektiven Darstellung von verbrückten Metallocenkomplexen mit unsubstituierten oder 2-substituierten Indenylliganden |
| EP1554297B1 (de) * | 2002-10-25 | 2006-07-12 | Basell Polyolefine GmbH | Racemoselektive herstellung rac-diorganosilylbis(2-methylbenzo¬e|indenyl)zirconium-verbindungen |
| DE10250061A1 (de) * | 2002-10-25 | 2004-05-06 | Basell Polyolefine Gmbh | Verfahren zur racemoselektiven Darstellung von isolierbaren ansa-Metallocenbiphenolatkomplexen mit kürzeren Isomerisierungszeiten |
| DE10250025A1 (de) | 2002-10-25 | 2004-05-06 | Basell Polyolefine Gmbh | Verfahren zur Darstellung teilweise hydrierter rac-ansa-Metallocen-Komplexe |
| DE10360060A1 (de) * | 2003-12-19 | 2005-07-21 | Basell Polyolefine Gmbh | Verfahren zur meso-selektiven Synthese von anso-Metallocen |
| RU2391350C2 (ru) * | 2004-07-02 | 2010-06-10 | Базелль Полиолефине Гмбх | Способ рацемоселективного синтеза анса-металлоценов |
| ATE547439T1 (de) | 2007-10-25 | 2012-03-15 | Lummus Novolen Technology Gmbh | Racemoselektive synthese von ansa-metallocen- verbindungen, ansa-metallocen-verbindungen, diese enthaltende katalysatoren, verfahren zur herstellung eines olefinpolymers durch verwendung der katalysatoren und olefinhomopolymere und - copolymere |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5489682A (en) | 1990-11-21 | 1996-02-06 | Massachusetts Institute Of Technology | Catalytic asymmetric reduction of enamines |
| JPH06502867A (ja) | 1990-11-21 | 1994-03-31 | マサチューセッツ インスティテュート オブ テクノロジー | 有機基質を接触還元するための新規の方法 |
| DE4431837A1 (de) | 1994-09-07 | 1996-03-14 | Basf Ag | Geträgerte Metallocen-Katalysatorsysteme |
| DE19741876A1 (de) | 1997-09-23 | 1999-03-25 | Basf Ag | Verfahren zur selektiven Herstellung racemischer Metallocenkomplexe |
| US6090961A (en) | 1998-07-09 | 2000-07-18 | Sumitomo Chemical Company, Limited | Method for producing titanium complex |
-
2000
- 2000-06-29 DE DE10030638A patent/DE10030638A1/de not_active Withdrawn
-
2001
- 2001-06-28 DE DE50102338T patent/DE50102338D1/de not_active Expired - Lifetime
- 2001-06-28 US US10/312,359 patent/US6992204B2/en not_active Expired - Lifetime
- 2001-06-28 BR BR0112050-6A patent/BR0112050A/pt not_active IP Right Cessation
- 2001-06-28 EP EP01965046A patent/EP1294734B1/de not_active Expired - Lifetime
- 2001-06-28 JP JP2002505794A patent/JP4454225B2/ja not_active Expired - Fee Related
- 2001-06-28 CN CNB018145639A patent/CN1267441C/zh not_active Expired - Lifetime
- 2001-06-28 AU AU2001285786A patent/AU2001285786A1/en not_active Abandoned
- 2001-06-28 ES ES01965046T patent/ES2219557T3/es not_active Expired - Lifetime
- 2001-06-28 WO PCT/EP2001/007389 patent/WO2002000672A1/de active IP Right Grant
- 2001-06-28 MX MXPA03000054A patent/MXPA03000054A/es active IP Right Grant
- 2001-06-28 AT AT01965046T patent/ATE267205T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1267441C (zh) | 2006-08-02 |
| DE50102338D1 (de) | 2004-06-24 |
| BR0112050A (pt) | 2004-02-10 |
| EP1294734A1 (de) | 2003-03-26 |
| EP1294734B1 (de) | 2004-05-19 |
| US20040010157A1 (en) | 2004-01-15 |
| WO2002000672A1 (de) | 2002-01-03 |
| DE10030638A1 (de) | 2002-01-10 |
| JP2004501928A (ja) | 2004-01-22 |
| ES2219557T3 (es) | 2004-12-01 |
| AU2001285786A1 (en) | 2002-01-08 |
| US6992204B2 (en) | 2006-01-31 |
| MXPA03000054A (es) | 2004-09-13 |
| CN1447816A (zh) | 2003-10-08 |
| ATE267205T1 (de) | 2004-06-15 |
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